Classifications

• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B81—MICROSTRUCTURAL TECHNOLOGY
  • B81C—PROCESSES OR APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OR TREATMENT OF MICROSTRUCTURAL DEVICES OR SYSTEMS
  • B81C1/00—Manufacture or treatment of devices or systems in or on a substrate
  • B81C1/00015—Manufacture or treatment of devices or systems in or on a substrate for manufacturing microsystems
  • B81C1/00206—Processes for functionalising a surface, e.g. provide the surface with specific mechanical, chemical or biological properties
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B82—NANOTECHNOLOGY
  • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
  • B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B82—NANOTECHNOLOGY
  • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
  • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
  • H10K10/701—Organic molecular electronic devices
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
  • H10P90/00—Preparation of wafers not covered by a single main group of this subclass, e.g. wafer reinforcement
  • H10P90/19—Preparing inhomogeneous wafers
  • H10P90/1904—Preparing vertically inhomogeneous wafers
  • H10P90/1906—Preparing SOI wafers
  • H10P90/1914—Preparing SOI wafers using bonding
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
  • H10W10/00—Isolation regions in semiconductor bodies between components of integrated devices
  • H10W10/10—Isolation regions comprising dielectric materials
  • H10W10/181—Semiconductor-on-insulator [SOI] isolation regions, e.g. buried oxide regions of SOI wafers

Definitions

• the present invention relates to new molecules capable of anchoring on a surface by means of at least one covalent bond and having a functional group enabling them to associate with at least one non-covalent type bond with an object or a functionalized surface by a molecule having a complementary functional group, and their applications.
• EP-A-0 943 158 discloses the use of self-assembly of complementary strands of DNA for the manufacture of devices in photonics and electronics.
• the reversibility of the interaction between the two molecular species involved in the assembly process is the determining factor that allows the "surface + object" set to find its optimal position which corresponds to the maximum number of binding interactions allowed by parameters such as the size and shape of the objects, the size and shape of the areas of the surface grafted by molecules capable of recognition, the surface concentrations of molecules able to self-assemble on the object and on the surface (or on a clearly defined area of this surface), etc.
• This method of placement and immobilization involves multiple molecular interactions between the surface of the first object and the surface of the second object, each of the surfaces preferably having compounds having moieties (groups) capable of recognizing each other.
• the present application relates to a method of placing and immobilizing (anchoring) a first object having a surface functionalized with compounds, preferably of small size, of formula I Y '(X% A 1 (I) on the surface of a second object having a surface functionalized with compounds, preferably of small size, of formula II
• a and A 'independently are functional groups capable of anchoring at least by covalently bonding to the surface of a given object
• X and X' independently are aliphatic, especially linear, branched or cyclic spacers and may comprise one or more heteroatoms, or aromatic, or heteroaromatic, or which may consist of several aromatic or heteroaromatic rings and optionally consist of alternating aliphatic chains with aromatic or heteroaromatic groups
• n and n 'independently have the value 0 or 1
• Y and Y are independently functions capable of generating one or more non-covalent type bonds, Y and Y 'being chosen complementary, namely allowing the creation of one or more non-covalent bonds or being chosen in such a way as to be able to complex an atom of metal or an identical metal compound.
• X and X ' are, for example, a divalent radical derived from an alkyl
• X and X ' are heterocyclic spacers, it is, for example, a 5- or 6-membered partially unsaturated heterocyclyl, unsaturated 5- or 6-membered heterocyclyl, unsaturated 9 or 10-membered fused heterocyclyl, lower cycloalkenyl or phenyl and in particular oxazolyl, isoxazolyl, thienyl, furyl, dihydrofuryl, pyrrolyl, pyrazolyl, thiazolyl, phenyl, isothiazolyl, benzofuryl, cyclopentenyl, cyclopentadienyl or pyridyl.
• X and X ' may in particular be an aliphatic chain which may contain one or more heteroatoms and optionally functional or non-functional side groups.
• This aliphatic chain can see one or more of its hydrogen atoms replaced by halogen atoms such as iodine and preferably bromine or chlorine, or deuterium.
• X and X ' are especially an aliphatic chain.
• this alkyl is preferably C 1 to C 15 , advantageously C 1 to C 2 , in particular C 1 to C 2
• C 10 particularly C 1 to Cs, in particular C 1 -C 5 linear or branched.
• X is in particular a divalent radical derived from a methyl, ethyl, isopropyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl.
• this alkenyl or alkynyl is preferably C 2 to C 15 , advantageously C 2 to C 12 , especially C 2 to C 10 , particularly C 2 to Cs, especially C 2 to C 5, linear or branched.
• X or X ' comprise at least one heteroatom, they advantageously comprise from 1 to 4, preferably from 1 to 3, in particular from 1 or 2, especially a single heteroatom.
• the heteroatom is selected from sulfur, nitrogen, oxygen and preferably one of the latter two.
• X and X ' preferably represent an alkyl radical and particularly an octyl or hexyl radical, especially a linear radical.
• the functional groups A and A ' are chosen according to the surface to be functionalized in accordance with the known functionalization of surfaces (Patterning Self-assembled Monolayers, Progress in Surface Science, 2004, 75, 1-68; Whitesides, Self-Assembled Monolayers of Thiolates on Metals as a Form of Nanotechnology: Chem Rev. 2005, 105, 1103-1169).
• a and A ' preferably represent a radical capable of creating one or more covalent bonds with the surface atoms of silicon and particularly a vinyl radical.
• Y and Y ' are functions capable of generating one or more non-covalent type bonds, and preferably hydrogen bonds.
• Y preferably represents a heterocyclic radical capable of generating at least one hydrogen bond and particularly a diaminopyrimidyl radical.
• Y ' may also be a heterocyclic but must be capable of generating at least one hydrogen bond with Y and particularly if Y is a diaminopyrimidyl radical, then Y' may be a 1,3-dioxoindole radical.
• metal atom is, for example, iridium or a metal compound containing, for example, indium.
• An example of a complementary functional group Y and functional group pair Y 'to allow the creation of non-covalent bonds of the hydrogen type is, for example, the pair 2,6-diaminopyrimidine and 1,3-dioxoisoindole (maleimide) establishing 3 hydrogen bonds ( two amino-oxo and one azo-azo).
• small compounds is meant a compound of molecular weight advantageously less than 3000 g / mol, preferably less than 500 g / mol.
• microelectronic devices such as thin chips of integrated circuits (for example in the control electronics of a microsystem) of the order of mm 2, in particular devices for Optoelectronics, especially AsGa stickers.
• S2 objects for example electronic devices, preferably microelectronic devices, particularly optoelectronic devices, particularly silicon wafers.
• These objects have a size typically between 1 micron and 1 mm.
• a compound of formula I is reacted with an object S1 and a compound of formula II with an object S2.
• the functionalization of the surface of the object S1 and the functionalization of the surface of the object S2 are carried out using techniques known to those skilled in the art. More particularly if the objects S1 and S2 are silicon substrates, then A and A 'will be able to create one or more covalent bonds with the surface atoms of the silicon and particularly A and A' will be vinyl radicals.
• S 1 and S 2 will be particularly carried out by hydrosilylation reactions and more particularly by thermal or photochemical hydrosilylation reactions.
• S1 and S2 there are two objects (S1 and S2) whose surfaces are functionalized by molecules comprising a group Y 'and Y respectively where Y and Y' are capable of generating at least one hydrogen-type bond between them.
• the compounds of formula I and II above have very interesting properties and qualities. They comprise at least one function enabling them to be covalently grafted onto a given substrate and also comprising at least one functional group making it possible to create at least one non-covalent bond with a compound having at least one complementary functional group.
• the method of the invention allows placement, precise orientation and immobilization of a specified number of nanometric to micrometric sized objects on the surface of a substrate.
• Dilution in functional groups Y (or Y ') within the layer may be carried out by diluting the compound A-Xn-Y (or A'-X'n'-Y') by mixing with a molecule of type A. -Xn or A-X'n '(not containing a function capable of creating non-covalent bonds) during functionalization of the surfaces.
• This technique makes it possible to precisely modulate the assembly forces by adapting the ratio between the molecules having a Y or Y 'group and the molecules that do not contain them.
• the modulation of the assembly forces is also possible by varying the surface concentration according to Y and Y 'by varying the size of the anchoring groups on the surface (A and A').
• the larger the size of the anchoring group the less molecules will be available on the surface and the less Y and Y 1 type functions will be available to generate non-covalent bonds.
• the advantage of using this type of link with respect to the literature resides in particular in the reversibility of the assembly process between the two objects S1 and S2.
• the assembly forces involved are furthermore variable by dilution, that is to say by varying the number of groups Y 'on S1 and Y on S2. (concentration of the molecules A- (X) n -Y and A '- (X) n -Y' on the surfaces).
• the attractive forces can be modulated according to the number of hydrogen bonds that can be created between the complementary groups Y and Y '.
• the different approaches and the choice of the functional groups allowing to modulate the assembly forces are presented p.3-31 and p.64-93 of Molecular Self-Assembly, Organic vs. Inorganic Approaches. Structure and
• the same surface may, in addition, be functionalized by different molecules A- (X) n -Y and A '- (X) ⁇ -Y' to allow the placement of different functionalized surfaces by means of specific molecular recognition.
• the method of the invention thus makes it possible to place objects with functionalized surfaces that can be of small sizes (in particular of micrometric or even nanometric sizes) on objects with a functionalized surface of a support such as a wafer.
• This method has applications in many fields such as, for example, the fields of microelectronics, biology, optoelectronics, etc.
• the use of the method of the invention for placing thin chips of integrated circuits for example the control electronics of a microsystem
• thin chips of integrated circuits for example the control electronics of a microsystem
• the method of the invention makes it possible to control the assembly forces between each functionalized surface of an object and the functionalized surface of the support on which the object is to be placed. It is thus possible from the same support to adjust according to the intended applications the assembly forces between the different objects and their support, these forces can then be identical for the different objects or different.
• the invention also relates to the use of compounds of formulas I and II above for the placement, orientation and immobilization of functionalized objects on functionalized surfaces.
• the method of placing and immobilizing (anchoring) an object on a surface according to the invention is advantageously used in the fields of electronics, biological engineering, devices microfluidics and microelectronics, photonics, optoelectronics, optics II is preferably not implemented in the field of medical diagnosis.
• the present application also relates to the novel compounds of formula I and II described above.
• the present application finally relates to objects S1 having a surface functionalized with compounds A- (X) n -Y and objects S2 having a surface functionalized with compounds A- (X) n -Y 'described above, as well as the combined objects comprising the objects S1 and S2 non-covalently linked by the compounds A- (X) n -Y and A '- (X) n -Y' described above.
• FIG. 1 shows the preparation of a compound of formula I or II (stage A), the functionalization of the surface of a first object by this method.
• a silicon wafer S1 and an inorganic semiconductor S2 are treated with a 2% solution of hydrofluoric acid for 1 minute.
• a glass tube In a glass tube is placed the silicon wafer S1 with a large molar excess of compound of formula II where A is a vinyl radical and Y is a diaminopyrimidine group (see Fig IB). The tube is then heated at 200 ° C. for 2 hours under argon. The silicon wafer is then removed and rinsed with various solvents (ether, pentane, dichloromethane, etc.). After sonication for 5 minutes in dichloromethane, the piece is removed and then dried under argon.
• solvents ether, pentane, dichloromethane, etc.
• the wafer and the inorganic semiconductor were assembled by mechanical placement in a suitable stirring solvent as described by Zheng, Adv. Funct. Mater. 2005, 15, 5).
• the self-assembly was done through three hydrogen bonds (see Fig II).

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• Engineering & Computer Science (AREA)
• Manufacturing & Machinery (AREA)
• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• General Health & Medical Sciences (AREA)
• Molecular Biology (AREA)
• Microelectronics & Electronic Packaging (AREA)
• Pyrrole Compounds (AREA)

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• 2005
  • 2005-06-15 FR FR0506088A patent/FR2887244A1/fr not_active Withdrawn
• 2006
  • 2006-06-12 JP JP2008516375A patent/JP2008546674A/ja not_active Withdrawn
  • 2006-06-12 WO PCT/FR2006/001323 patent/WO2006134260A1/fr not_active Ceased
  • 2006-06-12 EP EP06764772A patent/EP1890959A1/de not_active Withdrawn
  • 2006-06-12 US US11/916,392 patent/US8277599B2/en not_active Expired - Fee Related

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